What The Hell, Dude?
by Metamorphosis2011
Summary: It had only been a couple of words, thoughtlessly uttered, because quite frankly with Cas always pinching his stuff, he started running low on jeans and shirts. If Dean had known what he would start with those words, he would have shoved them right back into his mouth and gone shopping himself. Then again, maybe not. Maybe things turned out alright in the end.


**A/N:** Just something I knocked out this afternoon. I took my inspiration from the famous picture of Misha on the beach in a red blouse and colorful skirt that's been going around the internet forever and appeared on my tumblr dash one too many times for my mind not to take notice and go places ;)

I could totally see Castiel not give a fuck about norms and experimenting and going with what feels comfortable. I combined that with the canon knowledge of Dean's affinity for women's underwear and tada, have some PWP. I don't claim to know everything there is to know about this subject but hope I managed to do it justice, and at the heart of it is just a work of fiction, and it does have Dean in it who might have a slight fetish for men (Cas) in women's clothing. I hope you enjoy.

* * *

><p>"Cas, man, seriously, just go and buy yourself some goddamn clothes. You can't be wearing my cast-offs forever."<p>

"But I am perfectly content to -."

"Just do it!"

It had only been a couple of words, thoughtlessly uttered, because quite frankly with Cas always pinching his stuff, he started running low on jeans and shirts. If Dean had known what he would start with those words, he would have shoved them right back into his mouth and gone shopping himself. Then again, maybe not. Maybe things turned out alright in the end.

###

Dean was not able to keep the shit-eating grin off his face as he entered the kitchen where his brother was slaving over the stove, taking his turn at preparing breakfast for everyone.

"Nice one, Sammy!"

"Huh?" His brother grumbled not looking up from where he was watching the bacon fry.

"Didn't think you still had it in you, but wasn't there some kind of agreement on not bringing chicks back to the bunker?"

Now he had Sam's undivided attention as his head shot up and whipped around, looking more than just a little bit confused.

"AW, don't act all coy now." Dean's grin got even bigger and he waggled his eyebrows as he produced a pair of satin panties seemingly out of thin air from behind his back, twirling them in the air like some kind of trophy. "Just, since when are you doing your conquest's laundry? Man, she must have been good."

Sammy's face changed from confused to his patented 'Dean has finally lost it' bitch face, accompanied by "The hell you talking about?"

"Come on Sammy," Dean continued his tease. "I sure as hell didn't bring anyone round and unless Cas brought someone back to do the dirty with (and no, Dean did not want to think about that for too long), that leaves you."

Cas' ears must have been burning because he chose that very second to enter the kitchen, like he had been summoned, his eyes inevitably landing on the item of clothing in Dean's hand, still held high in the air.

"Man, I'm telling you-" Sam started but was cut off by the former angel.

"Why are you holding my undergarment in your hand?" He asked eyeing the object in question and Dean nearly choked on his saliva.

"What? I found those in the bathroom and-" He stammered, definitely not turning an interesting shade of red.

"Oh- I must have dropped them on the way to do laundry. Thank you for retrieving them for me." Cas walked up to Dean and plucked the item of out his (now trembling) hands, and turned on his heels walking out of the kitchen, mumbling something about having to do another load now under his breath.

Dean just stood frozen, shell-shocked unable to move as he tried to make sense of what had just happened. Now it was Sammy's turn to give him a shit-eating grin, as he tried to hold back the laughter but failed miserably chuckling manically.

Dean was sure his face was a nice shade of crimson by now. Did he just hold- how could- were they- did Cas really allude to owning this pair of panties and, oh my God- had he actually been wearing them? Maybe even just before he got in the shower this morning? Now his whole face seemed to be on fire. Fuck. And his stupid brother was still laughing his head off at his expense.

"Shut up." He snapped.

"Didn't say anything." The younger Winchester didn't even try to hide his glee at Dean's embarrassment and Dean could see the mouth opening, no doubt to come up with some smart-ass remark, and he really didn't need this now. He was feeling embarrassed enough for the both of them. So he hightailed it out of the kitchen towards his room.

Damn, but they were a nice pair of panties, if the belonged to a girl, that was. Satin with a little bow at the waistband and they were this deep shade of blue which probably would really accentuate Cas' eyes, and nope- derail that thought right there, Dean scolded himself. He was definitely not thinking about his best friend wearing panties. God when did it get so hot around here? Dean felt an urgent need to retreat to his room and regroup. Ideally with his laptop and a few of his favorite websites, just for reassurance.

#

Dean sat at the kitchen table, nursing a well deserved glass of bourbon. They had all taken a bit of a beating during their latest hunt. It should have been an easy salt and burn, something to show Cas the ropes of being a hunter. But as they so often did, things went sideways and the three spirits (not one like they had assumed) had left them all sore and bruised before they could get rid of them. He had sent his brother and Cas off to shower. In his case, cleanliness would have to come second to the company of the amber liquid, which he was in dire need of right now.

He was on his second generous helping and could start feel himself relax when Cas sauntered into the kitchen and Dean half choked, half spat out the gulp of whiskey he'd just tried to swallow.

"The hell you're wearing?" He stared at his friend like he had miraculously grown a second head, and quite possibly that would have been preferable.

"If I am not mistaken it is called a blouse." Castiel offered matter of factly as he pulled out a glass and grabbed the bottle off the table, pouring himself a generous helping.

"But- that's it's-" Dean stuttered like he had forgotten how to talk. But could you blame him? The _'blouse'_ Castiel had on had some kind of floral pattern on it and it was rather figure hugging. And to make matters worse, the man had left the top three buttons open, revealing a rather nice sliver of neck and collar bone, plus the damn thing was taken in at the waist and it stretched tight across Castiel's stomach and, nope. Dean had to avert his eyes.

"I do not understand? You were the one to advise me to get myself some clothes, and now you're complaining?"

"Yeah, _guys_ clothes, you know, shirts and jeans not - you do know that this is- for chicks?!" It was not really a question but at the same time it was because even Cas, angel turned human turned angel again, albeit powered down, should know the difference between dude clothes and chick clothes. And suddenly Dean's mind flashed back to blue panties and- oh shit, his face was heating up, _again_.

"I don't see the problem. You said to change into something comfortable, I find this very comfortable and- I like the colors. I did look at the male clothing, but it is so - limited." Castiel simply stated without as much as a shrug as he sat down opposite Dean, knocking back the contents of his glass in one big gulp.

"Where you even get this shit from?" Dean knew he should keep his trap shut, but curiosity got the better of him.

Cas quirked an eyebrow at Dean, looking at him like he suddenly must have gone stupid. "It's called a department store, and they have a wide selection of clothing, you should go one day." He said so condescending, that Dean just knew he was trying to get a rise out of him, but he wasn't gonna take the bait while he had other thoughts on his mind.

So he just rolled his eyes. "Not what I meant, I mean, did you really just walk into the women's section and-"

"Well, they did seem a bit confused initially, but one of the ladies was very helpful once I explained the situation to her."

"Ok, whatever." Dean shrugged cutting his friend off, realizing that really, he'd rather not have this conversation, despite in a way wanting to admire Cas and his 'no care' attitude. But imagining the man trying on a variety of clothes in the changing rooms, he was not gonna go there. _And_ he definitely did not stare at that slither of revealed skin for longer than was considered appropriate, and just for a second thinking that yes, the color did in fact look good on his friend. He _most_ definitely did not feel his pulse speed up the longer he stared or his hands go clammy or his breath starting to hitch as Castiel shifted, pulling the offending item of clothing down slightly on one side, revealing more of his collarbone! That would be ridiculous, it was only Cas' neck after all and- Dean swallowed back the sudden lump in his throat. There was no way he was entertaining these kinds of thoughts with regards to his friend. He hadn't in the past and he definitely wouldn't allow himself to now. What the hell had gotten into him?

Drink, and lots of it, definitely seemed like a great idea just about now, so he refilled his glass, mock toasted to his friend and downed the whole lot before heading to have that suddenly very urgently needed, and preferably very cold, shower.

#

"No way," Dean protested so loudly that out of nowhere Sammy miraculously appeared on the stairs, drawn out by the commotion. "I'm not taking you with us looking like _that_!"

Sam's gaze flitted between his brother and the angel, nervously observing the stand-off. He didn't need to ask what this was about as Castiel, or more precisely, the clothes he was wearing, spoke for itself. He was cladded in what was unmistakably a pair of black women's trousers, the material soft and flaring out at the calves, combined with a simple but tailored button down shirt, shades of blue flowing together to give some kind of marble effect and ending just above the hips, leaving a small portion of his stomach exposed. Sam had to admit that it did not altogether look too bad, just kind of off on a dude. At least the guy had taste. He seemed to have developed a preference for what would be best described as 'Baby Blues' and at the moment they complemented the furious color of his eyes perfectly.

As far as Dean and Cas were concerned, Sam realized he might as well be invisible as they didn't even acknowledged his presence, but continued their stare-off. Cas eventually broke the all too tense silence. "Dean, I understand your need for me to adhere to gender norms, especially when we're out working a job, and you never had reason to argue with me over my appearance. But this is, as you tend to call it my 'downtime', and I just want to be comfortable."

"Well, then be comfortable in something else." Dean huffed back, lost for something better to say.

"Why?" Castiel took a step closer, now nose to nose with Dean, challenging the hunter with both words an stare.

"Because-" Dean gulped, licking his lips in a gesture way too vulnerable and out of place for this situation. He gulped, trying to reign in his emotions, throat suddenly gone dry. "Because- people will make fun of you, ok?" He gritted out eventually, not quite able to hold his friend's gaze. Doing whatever it was that Cas needed doing in the safety of the bunker was one thing, but to take this out into the real world, with all its nastiness which maybe Cas just hadn't experienced yet, was taking it a step too far.

Cas took a step back, looking hurt, and damn, Dean did not want to put that look on the former angel's face but sometimes the truth had to hurt and better from him than from some backwater redneck out there.

Cas quickly composed himself again. "I do not wish to join you any longer. Just answer me this Dean, are you really that concerned about my safety or more about what people might think of _you_?" Cas' accusing tone had Dean flinch.

Castiel turned on his heels and stormed in the direction of his room. "Cas, wait-" Dean called out, trying to get his friend's attention but to no avail. He stared for a long moment at the space Castiel had inhabited only a few seconds ago and let out an exasperated sigh. Damn, that should have gone better.

"Dean, man. Really?" Sam's voice broke him out of his thoughts.

"What?" He snapped defensively, because Cas had hit a raw nerve, and he hated himself for it, and definitely didn't need to be called out on it by his little brother. But of course he couldn't let it rest.

"That was low."

"You know it's the truth though, so don't gimme that." Dean grumbled, defensively.

"Still, he has a point, doesn't he? Are you really so worried about him or more concerned about your male ego getting bruised? You know Cas is quite able to look out for himself."

"Fuck you," was all the answer Sammy got before Dean stomped off to his own room. This evening was already ruined, he definitely didn't feel like going out any more.

How dared Sammy! Yes, ok, he would be a bit embarrassed being seen with Cas dressed like that. But that was not even it. _That_ his male ego, as his brother so poignantly called it, could handle. The way Castiel dressed and presented himself, was starting to get to Dean in a way he was most definitely not comfortable with, unnerved him in a way he'd rather not address. He had no idea what to do with that information and this whole mess was definitely not helping his already confused emotions with regards to his friend. So when he saw Cas dressed up like that to the nines, he'd snapped, his well built facade crumbling fast.

He had managed to keep his feelings all nicely under wraps for so many years, why was it suddenly getting so hard to keep the man strictly in his friend-zone? Dean let out an exasperated sigh. Damn those fucking blue panties and his own secret panty kink. He was sure that was when it all started to go to hell.

#

So this was weird. Definitely not his usual haunts, but sometimes you had had to take one for the team, and that was how he ended up with his brother and best friend in a gay bar, attending their monthly drag night. It had been Sam (of course it was Sam's idea, he was the smart and intuitive one after all) who had come up with the idea and after some quick research on the internet found just the spot, merely an hours drive from the bunker, for them to head to on a Saturday night.

Dean would be lying if he said the idea didn't initially freak him out, but Cas had sounded so excited at the prospect and Dean still felt like crap after the fallout, that he couldn't help but say yes to the outing. At least no one should look at Cas (or him) in a funny way here. On the contrary, people were eying his friend with a hungry glint in their eyes that was very familiar to Dean, and made him uncomfortable and growing hot under the collar for reasons he really did not want to dwell on.

Castiel sat between the brothers, eyes wide as saucers as he studied with increased fascination the people in their various outfits and hair and makeup that paraded on stage. Compared to all the makeup and sequins and shiny fabric Dean was blinded by, his friend was dressed rather conservatively in a charcoal pantsuit, the blazer of which he had discarded on entry, under which he had on another one of his favorite blouses, this one in shades of pink which shouldn't work but even Dean had to admit kind of did. He had not dared to check the angel's footwear, but as Castiel appeared taller than normal, Dean suspected there were some form of heels involved.

Sipping on his beer, he had long lost interest in the proceedings on stage and had taken to study his friend with renewed interest, a warmth pooling in the pit of his stomach which he soundly attributed to the alcohol and not to any fondness with regards to the dark haired man.

Dean had thought a lot about him ever since their argument. He didn't get it, why Cas was like that, preferred to dress in a way that seemed so against everything Dean had ever known to be 'acceptable'. Of course he was not stupid, he knew sometimes dudes liked dressing up but he more associated that with the likes of those larger than life drag queens that were currently parading on stage. Cas, in contrast, was just content to wear everyday clothes, that just so happened to be made for women

A lot of contemplation during this last week had him come to the conclusion that maybe he didn't need to get _it_ in order to be ok with his friend liking women's clothes. Dean had been trying to find a box in which Castiel might fit, but found none. Then again, he was an angel, there might just not be a box big enough to hold him. He glanced over at the man in question with a fond smile, before catching himself doing so and staring at the beer in his hand instead.

He was trying to reconcile his image of the angel, soldier and one tough son of a bitch with the man sat across from him but time after time drew a blank. Was Cas like those guys up on stage? Would he eventually want to dress up in sparkly dresses, wearing wigs and make-up and, did that imply that he was now into dudes? Dean had more questions than answer and really didn't know enough about this to figure out how this was supposed to work, and that freaked him out, because he needed parameters to work off.

A confused and slightly irked Dean had left the bunker that evening but an utterly confused and mortified Dean returned that night, retreating to his room quickly with a bottle of Scotch, leaving Sam and Castiel to chat in the kitchen, as he tried to not make sense of why this was all getting to him so much and of any possible implications.

#

Dean should have known better. Should have seen the big neon warning signs that had been flashing above his head ever since that evening at the bar, but why address something when you can simply ignore and suppress. Cas, unknowingly had helped. As they had a busy few weeks case-wise, he mainly kept to his 'work clothes' as he had come to call them, making it easier for Dean to go back to the way things were before. This version of Cas, Dean was able to compartmentalize and ignore when need be. That was why he was totally caught unaware when the dark haired man walked into the kitchen in what was unmistakably a silky red wrap around skirt.

"Oh, for fuck's sake!" Dean exclaimed in sheer and utter frustration, while at the same time not being able to pull his gaze away. There was something mesmerizing about the way the light fabric clung to parts of Castiel's frame while flowing freely at others. The way it hugged his ass just right, Dean's eyes tracing the nice curve of the man's backside, following the line down to where the skirt stopped just above the ankle, revealing just the slightest bit of Cas' hairy legs and ankles. Dean stopped there for a second, he had no idea why but he had assumed Cas might shave his legs but this, the weird combination of soft fabric against hairy legs, feminine against masculine, had Dean come out in a sweat and, shit he could definitely feel his pants grow tight at an alarming rate.

Cas turned around and pierced him with a condescending glare, which did not help, not at all, as now Dean could see the slightest outline of a protuberance of where the fabric clung snugly to Castiel's crotch area, and he jumped up, freaking out, needing to get as far away from Cas as he could, right the fuck now. He desperately needed some space to calm down. But apparently God did not hear his prayer (and why did that not surprise him), as Castiel, clearly irritated by Dean's behavior, chose to follow him, and came bursting through the just closed door with a fierce look on his face.

"What is your problem, Dean? I thought you said you were ok with me." He yelled, accentuating the 'me' with a wave of his hand over his body.

And Dean could feel the damn, break, had felt the pressure build for weeks and weeks, had tried to patch up the holes as they appeared but apparently it had all been for nothing as his facade crumbled right in front of him.

"You don't fucking get it!" He shouted, past caring for the consequences. "

Cas stood in the middle of the room, all fury having been replaced with confusion and curiosity as he stared at the man opposite him. "What don't' I get?" He still tried to put some indignation into his voice because at the core of it, he had a feeling that this was still all about his way of expressing himself. God, he had believed that Dean started to understand that he just didn't care about gender norms and that his friend even was making tentative steps of accepting him for who he was. Clearly he had been wrong, and it hurt. He had never let himself hope for more than friendship with the hunter but to realize that even that came with strings attached, was too much.

Dean let out a desperate sigh, that turned into a hiccup half-way.

"You have no idea what you are doing to me, do you?" Dean went for broke as he closed the distance between them with a few steps, taking Castiel's hand and pressing it against his crotch.

Cas' eyes grew wide as he felt the hardness under his palm.

Dean's head fell against the other man's shoulder, taking in a calming breath. "This- this is how _ok_ I am with you. What you expect me to do about that?"

"_Oh_," Castiel could feel a shiver course through his whole body at those words, the way they were near whispered into his neck. The feel of Dean's erection under his palm had his own cock twitch, and Castiel instinctively rocked against Dean's thigh, with a desperate "Dean" on his lips, trying to make sense of the situation.

Dean sucked in an astonished breath at the motion, a moan escaping him as his head snapped up and green eyes met blue. Cas stared back, full of wonder and desire and Dean didn't know anything anymore, not even why he had been fighting this for so long. The way Cas ate him up with his eyes had Dean come out in goose-bumps and his stomach flutter excitedly. All his blood was diverted south, leaving him fully hard and panting and light-headed. Part of him still wanted to run but he was drawn in by Cas' eyes, always his eyes, and then it was Cas who closed the final distance with a needy sigh.

And thank God for that, as Dean was not sure he would have been able to make that decisive move, still having been too caught up in just drinking Cas in. But as soon as their lips met Dean's brain short-circuited, grabbing Cas rough around the waist and pulling him in close, needing desperately to touch, his hands running up and down the other man's waist and thighs, reveling in the feeling of the fabric against bulk and muscle, so unlike what he was used to, but so much better than he could have even imagined. Cas turned the kiss from questioning to decisive, opening his mouth, his tongue flicking out to lick at Dean's bottom lip before sucking it into his mouth, making the man shudder.

Dean grunted hungrily and whirled the angel around smashing him into the wall with slightly more force than necessary but Cas didn't seem to mind. On the contrary, the man was moaning his name and reaching back with one of his arms to draw Dean in closer, pulling him against his neck, urging him on with whimpers. Dean forgot how to form sentences then, just whined his agreement as his lips attached to the skin just behind Cas' ear and started to suck with a brutal force that had Cas writhe under him.

"Cas." The word was spoken almost reverently as his tongue teased gently against the mark he just left. It was in stark contrast to Dean's hands frantically and roughly roaming the body of the man he was pressed against, before gripping the skirt and bunching it up, lifting it up enough for him to palm at Cas' ass and when he felt the unmistakably soft fabric of panties, Dean lost it.

"Oh fuck," was all he was able to say as he quickly pulled the skirt up all the way, feeling his dick swell even more at the sight of those blue panties, sat snug against Cas' ass.

"Cas wiggled his hips suggestively. "You like that?" He teased which earned him a slap to his right cheek. Cas couldn't hold back the groan at the sensation.

"You're killing me here, man." Dean whined as he popped his button, needing to free his aching cock. He unzipped his trousers pulling them down with his boxers to pool around his ankles, never breaking eye contact with Cas who was watching him greedily over his shoulder.

"Hands on the wall." Dean grunted as he pushed Cas' skirt all the way, leaving it in a bunched up mess around the man's waist. The dark hair man obeyed instantly, hands hitting the wall as he shifted back enough to be able to do so, in the process pushing his hips and ass out more.

He heard Dean grunt, before feeling urgent hands grab at the panties and pulling them to one side, palming the cheek and pressing some heated kisses against the skin which had Cas mewl and beg for more, which Dean eagerly provided, worshiping Cas with his hands and tongue until he just couldn't take it any more. The hunter gave his hard and leaking cock a few strokes before lining it up against Cas ass.

Cas took in a surprised gasp as the blunt tip pressed against his creek, where his panty was still half caught in he way. He pulled away ever so slightly. "Dean, don't we need -"

"Trust me, Cas," Dean said soothingly, letting his tongue lap over the skin of Cas' back where he had pushed his blouse up enough to be able to get to the delicious skin.

Before Cas could reply he felt Dean's cock slide down from his creek and between his thighs, Dean grunting as he shoved between them. Cas gasped when he felt the tip nudge his balls as Dean thrusted in.

"A bit closer together." Dean instructed, patting the sides of Cas' thighs before grabbing on tight to the man's hips, sighing with pleasure at the now increased tightness and pressure. His cock rubbing up against the panties added an intense sensation which threatened to quickly drive him to the brink. But Dean didn't care, in fact he welcomed it, as he continued to pull and push and thrust and shove and a frantic rate, clinging desperately to Cas, one hand tight on his hip while the other roamed over the skirt and blouse before finally reaching around and grabbing Cas' hard and leaking cock through the fabric of the panties, palming it in time with his thrusts.

"Oh god, Dean. More!" Cas whined shoving back against him, while trying to hold steady against the walls with his arms, which was quite a feat at the rate Dean was ramming into him.

"Cas, oh god Cas, so close." Dean grunted, feeling the build-up low in his gut, that tell-tale tingle, balls drawing tight. The combination of friction and years worth of pent-up sexual frustration with regards to his friend, to finally have him here like that, panting and desperate, had him come but a moment later. He shuddered as his cock spurt out streaks of come between Cas' thighs. The feeling of Dean's come and the continued strokes of his length had Cas come shortly after, shooting his load into his panties, where Dean's hand was still on him, his knees buckling for a second, as Dean's weight against him temporarily became too much.

They stood there, pressed tight back to chest, panting hard as they slowly came down from their respective highs, neither quite believing that this actually just happened.

Eventually Cas turned around, nervous what he might find in Dean's eyes. But Dean just smiled that beautiful lazy, fucked out smile and pressed his lips to Cas' in a deep gentle kiss that to Cas was more meaningful, more intimate, than what they had just experienced together. He sighed happily, pulling Dean in closer.

Neither of them wanted to speak, so they continued to make out until the mess they had left between them became uncomfortable and Dean ushered Cas out to have a shower and change into something 'nice', not before giving him one last bruising kiss.

Dean felt a nervous anticipation build now that the high of his orgasm had worn off. He knew they had to talk, had to make sense of what had just happened and where that would leave them. Personally, he would have to face the fact that he was not as straight as he had always tried to believe and as for the way Cas' choice of clothes seemed to turn him on just that extra bit, he definitely would worry about that another day.


End file.
